Those Are The Rules
by Thirst4Chicken
Summary: Young trainer Gwendolyn is forced to pay more than money after losing a Pokemon battle to a veteran trainer who has had a very bad day. Original Characters, no background necessary. Strong M rating.
1. Route 1

" **Those Are The Rules"**

Reynard hated Viridian City and every motherfucker who lived there.

Born and raised in Pewter City, Reynard had never had occasion to visit Viridian City until this point in his life. He had started his Pokémon journey a little over a year ago, shortly after graduating from high school, having set out with nothing but two Nidoran and $500 to his name. Now he had collected over one hundred different species of Pokémon, carried over $10,000 around with him at all times, and was one of Kanto's rising stars. He had arrived in Viridian City with a single goal in mind: to defeat the local Gym Leader so he could collect his eighth and final badge and _finally_ make his way to the Pokémon League.

The only problem was that the Viridian City Gym Leader was nowhere to be found. The doors to the gym were locked, the place looked abandoned, and none of the locals even knew who the Gym Leader was, much less _where_ he was.

 _What the hell kind of city is this?_ , Reynard thought angrily as he began making his way back towards Pallet Town in hopes of finding an inn. _Nothing but old men trying to teach me how to catch Pokémon I already have and brain-dead townsfolk who don't even know who their own Gym Leader is. No wonder everyone is moving to Johto._

The sun was setting and Reynard was tired and cranky by the time he reached Route 1. The first thing he did was spray himself with a Max Repel before setting foot in the tall grass. It wasn't that he was scared; he had six trained Pokémon with him, after all, all over level 60, but he was in no mood to battle or be ambushed by a wild Rattata. Content that there were likewise no trainers in sight, Reynard began his short trek.

 _Just a little farther_ , he told himself. _I'll find an inn, get a good night's sleep, and then come up with a plan in the morning. Nothing but smooth sailing from here on out._

"Hey, you! I challenge you to a battle!"

 _Son of a bitch!_

It was a girl, about fourteen years of age, with bright red hair and a few freckles scattered across her face. She was wearing a (rather tight) black T-shirt and a checkered skirt that ended above her knees, leaving much of her legs bare and revealing a pair of tennis shoes as red as her hair. She worse a backpack, as most trainers did, bright pink and contrasting with her black top.

Were the circumstances any different, Reynard might have been intrigued. He liked redheads, he liked girls in skirts, and he liked them young; this girl looked like she check both of those boxes. She was objectively cute, too; her confident smirk, her bare legs, the slight curve of her hips, what looked like B-cup breasts…

Unfortunately, Reynard was tired and angry and cranky, and most certainly did _not_ want to battle, even if it was with an attractive teenage girl.

"Look, can we just skip it?" Reynard asked once the girl came to a stop in front of him. "I've had a really long day and I'm really tired and I just want to go to sleep."

"What's the matter, afraid I'm gonna beat ya?" asked the girl, smirking all the while.

"Kid, you have no idea who you are messing with," Reynard told her.

"You can tell me your name after I knock out your Pokémon and take half your money," responded the girl, cocky as ever. "My name is Gwendolyn, and I know the rules, okay? You can't refuse a direct challenge from another trainer. One on one, winner gets half the money of the other."

Reynard sighed wearily. "I know the rules. How about this: if you want to get your ass kicked that bad, I promise I'll fight you in the morning, okay? Deal?"

"No deal," said Gwendolyn. She smirked again, cocking her hip out and placing a hand on it as if showing off. "I'm short on cash and I need the experience. Either battle me or I get _all_ your money. Those are the rules."

Reynard sighed again. "You sure about this?"

"I'm sure," said Gwendolyn. "The rules are the rules."

 _What the hell_ , Reynard thought. _It will be worth it to at least wipe that stupid smirk off her face. Might even get a few bucks out of it._

"Alright, kid, you win," he said, stretching slightly as he pulled out his first Pokéball. He took several steps backwards in order to leave room for them to battle. "Let's get this over with."

Gwendolyn's only response was to pull out a Pokéball of her own and toss it into the space between them. There was a flash of light as the ball opened and revealed…

A Jigglypuff.

 _What?!_

"Um, Gwendolyn, was it?" Reynard asked.

"Yeah?"

"Exactly how long have you been a Pokémon trainer?"

"Um…what time is it?"

"I dunno, almost eight?" Reynard responded.

"Then about ten hours," Gwendolyn told him with a smile. "That's why I challenged you! Jigglypuff is my very first Pokémon, and I'm tired of fighting nothing but Rattata and Pidgey. I want a _real_ challenge!"

 _By Arceus. This is gonna be a bloodbath._

"Well, alright," said Reynard as he released his Nidoqueen. "But you asked for this, kid."

The battle (if it could even be called that) was over before it began. Gwendolyn's Jigglypuff only had enough time to lightly smack its opponent before Reynard's Nidoqueen wordlessly stomped the damn thing into the ground.

"I…I lost?" Gwendolyn asked, her eyes wide with disbelief as she returned her unconscious Jigglypuff to its Pokéball. "But how? How?"

"My ten months beats your ten hours," Reynard said tiredly as his Nidoqueen obediently returned to its Pokéball. "I did warn you, kid. Now, come on, pay up. Half your cash. Then I can finally get some sleep."

Gwendolyn blushed suddenly and looked away, as though out of embarrassment. "Um, about that…"

 _Oh, here we go…_

"You don't have any money, do you?" Reynard asked.

Gwendolyn slowly shook her head.

"Great," Reynard commented. This day just kept getting better and better. "You threatened to take all my money if I refused to battle you, and now you can't pay me when I beat you? You know what the rules say about that, Gwendolyn?"

"We…pretend this never happened?" she asked with a small smile, trying to act cute.

"It means I have to report you to League authorities and get your Pokémon Training License revoked," Reynard told her, growing angrier with every word.

Gwendolyn paled. "No, please don't!" she begged, walking over to Reynard and stopping right in front of him with tears in her eyes. "Please, please, I just got my Jigglypuff, I don't want to give her up already! I…I…it was a mistake! Please forgive me!"

"It's not a matter of forgiveness," Reynard reminded her. "I don't have a choice. It's like you said…those are the rules."

With that, Gwendolyn fell to her knees and began to sob right in front of Reynard, causing the young man to roll his eyes. The girl threw her head in her hands and began to cry, her legs folded under her checkered skirt, as Reynard stood there awkwardly.

Reynard knew he was being harsh; while the rules were clear about reporting trainers to the League, it was also true that few people ever took the rules completely seriously. Likewise, Gwendolyn had been a trainer for less than a day, which meant leniency would almost certainly be granted.

But he had _warned_ her, damn it, and she hadn't listened! He was having a bad day and she came along and tried to make it worse! She challenged him; she threatened him! Rules or no rules, she deserved to be punished.

 _But there are other forms of punishment_ , Reynard realized with a grin as he looked down at the girl crying on her knees in front of him. Suddenly he remembered her bare legs, her tight shirt, her short skirt, her nubile young form, the way she had smirked at him with her hip cocked out like she knew she was hot stuff…

"Look, there is _one_ way you can get out of being reported," he finally said, rolling his eyes as he did so, as if pretending he was doing the girl a favor.

The crying stopped almost immediately.

"R-Really?" Gwendolyn asked, her looking up at him from her knees with wide eyes. "You mean…you don't have to report me? I can keep my Jigglypuff?"

"That's right," Reynard told her with a small smile as she wiped the tears from her eyes. "According to the rules, if the loser can't provide their share of the winnings, they can compensate the winner by giving them something other than money, something worth half of however much the winner is carrying – whatever I would have had to give you if I had lost."

"I forgot about that!" Gwendolyn said, now smiling gratefully and standing back up. She looked like she was about to kiss Reynard out of happiness, or at least hug him; if his plan worked, she would be doing a lot more than that by the end of the night. "So how much do you have?"

Reynard grinned and showed her his Trainer Card. "$10,000. Which means you owe me something worth…"

"$5,000," Gwendolyn responded, her expression falling and the tears coming back. "But…but I don't have anything worth anywhere near that much! What could I possibly give you?"

Reynard took the time to look her up and down before smiling yet again. "Actually, Gwendolyn, I think I know _exactly_ what you can give me…"

"Uh! Uh! Uhn! Ohhh!" Gwendolyn moaned and groaned each time Reynard thrust into her adolescent pussy, seemingly burying his adult cock deeper and deeper into her nubile young body every time he pushed into her. "Oh, Arceus! Arceus!"

Half an hour had passed since Reynard and Gwendolyn had agreed to their 'deal,' and the fourteen year old girl was now lying naked on her back in the tall grass as Reynard practically pinned her to the ground and fucked the holy hell out of her. Gwendolyn's shirt and bra had been tossed aside, revealing her beautifully round B-cup breasts as they bounced up and down with each thrust, her nipples hard and pointed against the cool night air. Her skirt and panties had likewise been removed so that Reynard could shove his thick cock into her tight little cunt, her naked legs quickly wrapping around his thrusting hips. She was as naked as the day she was born, save for her bright red tennis shoes, which Reynard had insisted she keep on.

Gwendolyn had been hesitant of the entire deal at first, of course, but she loved her Pokémon and she loved being a trainer and she was _not_ going to lose her license within twelve hours of having earned it. As such, perhaps despite her best instincts, she had agreed to Reynard's terms; those being, he promised not to report her to the League so long as he was allowed to fuck Gwendolyn any way he wished for as long as he wished.

(Reynard's exact words were something along the line of "I want to be able to fuck every hole you have as many times as I want," which worried Gwendolyn a little, as she wasn't entirely sure which 'holes' he was referring to other than her mouth and pussy, but was sure she would learn by the end of the evening.)

Gwendolyn had actually started off the evening's activities by trying to suck Reynard's dick, but within minutes it became apparent that she was too inexperienced to do it properly. She had trouble fitting her whole mouth around his cock, to begin with, and she tended to gag no matter how much of his meat she managed to stuff in her mouth. As such, it wasn't long before most of her clothes were removed and Reynard was pushing her onto her back and spreading her legs for the 'main course.'

It had been difficult for Reynard to fit the entirety of his cock inside Gwendolyn at first, this evidently being her very first time. She had teared up a little as he pushed into her, inch after painful inch until he was buried balls-deep inside her, but she refused to do scream or cry or do anything but grip onto him a little bit harder each time he plunged into her virgin canal. In no time at all, he was pounding into her without any remorse, and she was bucking her hips to meet him thrust for thrust.

She was good, Reynard had to give her that; she took his dick like a champ and managed to bite off most of her screams of pain, meaning the only sounds she did let escape were mostly squeals of pleasure or moans and groans as each of his thrusts knocked the air out of her lungs. He took his time in admiring her form as he did his level best to ruin it; her rhythmically bucking hips, her beautifully bouncing breasts, even her flushed face as she closed her eyes and tried to wish it all away, or else pretend it was the man of her dreams making love to her, rather than some random stranger with a thing for younger girls.

"You feel _so_ fucking good," Reynard commented as he reached down to grope one of the girl's naked tits, squeezing it painfully hard as the other continued to bounce with every thrust. "You sure you've never done this before?"

"Nuh…nuh…never!" Gwendolyn gasped as she felt her legs tighten around Reynard's thrusting hips waist, his hips slamming against hers over and over and over again. "You're my…first! I was wuh…wuh…waiting! For suh…suh…someone special!"

 _This probably isn't what she had in mind,_ Reynard thought to himself as he shoved his cock as deep into Gwendolyn as he could, relishing in the feel of her wet cunt tightening around his throbbing length. _Hey, at least I'm not in such a bad mood anymore. Maybe all I needed was a good fuck after all._

Reynard had banged his fair share of girls and women since his journey began – including a certain swimsuit-clad Gym Leader from Cerulean City – but Gwendolyn was, by far, the _tightest_ and _sweetest_ he had ever had.

Well, her body was, at least. Gwendolyn was still a bit of a spoiled brat.

"Ouch! That – uhn! – hurts!" Gwendolyn whined as Reynard released her breast and instead reached down to squeeze her ass. "P-P-Please, don't…be so…rough! Uhnn!"

"I can be as rough as I want," Reynard reminded her. He tightened his grip on her ass and lifted her off the ground as he jackhammered into her, causing her to scream into the night. "You're gonna earn every single cent of that money you owe me."

"Aah! Aah! Aahn!" Gwendolyn cried out. It felt like his dick was pounding directly into her womb, smashing into her cervix and going all the way into her stomach! It hurt, but it hurt _so good_ that she couldn't help but love it even as she hated it.

Both Reynard and Gwendolyn lost sense of time as they rutted away in the tall grass, with Gwendolyn repeatedly being pushed into the grass and dirt as Reynard relentlessly pounded her tight pussy. It certainly wasn't what Gwendolyn had been expecting for her first time, but she tried not to think about that as the man above her groped her breasts and thrust into her cunt like it was his own personal property. She was simply doing what she had to do.

Those were the rules, after all.

"Fuck!" Reynard finally grunted following a particularly deep thrust into Gwendolyn that resulted in her cunt tightening around him like a vice grip. "I'm gonna cum, kid!"

"Nuh, nuh, not in me!" Gwendolyn begged as she tried to unwrap her legs from around his thrusting waist. "P-P-Please don't cum in me! I don't – uhn! – want to get pruh, pruh, pregnant!"

 _Probably a good call,_ Reynard agreed. _Don't want a pregnant teenager on my conscience._

As such, Reynard smashed his hips into Gwendolyn's a few more times, not just to savor the feeling of her cunt wrapped around his cock but also to make sure she was sore enough afterward to remember him, before pulling out and throwing her back onto the ground. Within seconds, he was exploding all over her, smiling as he watched his cum cover her breasts and then splatter all over her flushed face.

"Ooooh," Gwendolyn groaned as she felt the last of Reynard's hot cum spurt all over her face and tits. Her legs and hips were sore, but not nearly as sore as her formerly virgin pussy, and the feel of warm cum on her naked skin was almost soothing compared to the pounding she had endured.

"Damn, that was good," Reynard commented as he sat back and stretched his arms and back out. He smiled as he watched Gwen sit as well, groaning to herself as she wiped some of his cum off her face and tits. "What about you, kid? You having fun?"

Realizing the fate of her future as a Pokémon trainer was still in Reynard's hands, Gwendolyn did her best to smile a little as she nodded her head. Despite the fact that every muscle in her body was sore and throbbing, she found her pussy rather missed the presence of Reynard's cock, as though she suddenly felt empty without him there.

It was odd; no matter how much she told herself she didn't want this, no matter how much she supposedly despised the fact she had sold her body to a stranger to cover a debt, a part of her already missed having Reynard balls deep inside of her. Her cum-covered tits ached for further stimulation, her mouth watered at the sight of Reynard's surprisingly still erect penis, and her pussy was practically begging to be filled again.

 _What is happening to me?_ , she thought as she licked some of Reynard's cum off her lips.

"So…you promise you're not going to report me?" Gwendolyn asked hesitantly.

"Hand to Arceus," Reynard responded with a smile. "Alright, I'm good to go again. Get on your hands and knees, kid, I wanna see that ass of yours."

"What…again?!" Gwen asked, her eyes widening as Reynard helped her turn around and then pushed her over so she was standing on her hands and knees, bent over with her adolescent ass on full display. "But, but…we had a deal! You said – "

"I said I wanted to be able to fuck every hole you have as many times as I want," Reynard reminded her as he crouched behind her, immediately taking her young asscheeks in his hands and groping them fondly. "That was just round one, kid. We can do this all night if I feel like it. Those are the rules, after all. You aren't going back on our deal, are you?"

"No! I promise!" Gwendolyn said quickly before gasping as she felt Reynard pushing the head of his cock against her sore cunt once again. "It's just…I'm sore. Down there. You're hurting me. Couldn't we take a break? Or…or do something else?"

Reynard already had the head of his cock fully inserted into Gwendolyn's tight little pussy and was about to start pushing in the rest of his length when she made her offer. He paused with half his dick inside of her, one hand already reaching up to grope her perky breasts before he started pounding the hell out of her.

"Something else, huh?" He smiled cruelly as an idea occurred to him. "Yeah, sure. We can do something else."

Gwendolyn sighed in relief as she felt Reynard slowly pull his cock back out of her sore pussy. "Oh, thank you, it was just really starting to hurt, but I swear I caaaaaAAAAAHH!"

The girl's sudden scream was caused by the fact that, instead of stopping entirely as Gwendolyn had been expecting, Reynard had placed his manhood against her puckered anus and then pushed until the entire head of his cock had disappeared into her previously unpenetrated asshole.

"UUUUHHNN!" Gwendolyn groaned in pain, her eyes wide and her face flushed as she felt the intruder in her bowels. "Oh, Arceus! No, no, not there! P-P-Please not there!"

"Well, you said your pussy hurt. And what did you think I meant by 'every hole you have?'" Reynard questioned as he only continued to sink himself deeper and deeper into the girl's tight little ass, each and every movement accompanied by another groan of pain and discomfort. "Look on the bright side, kid, this way I can cum inside you as much as I want and you won't get pregnant. Everybody wins, right?"

Gwendolyn's only response was to bite off yet another scream as she felt inch after inch of Reynard's dick push itself deeper and deeper into her virgin ass. She clutched the dirt and grass beneath her with everything she had, her knees and elbows shaking from the effort it took just to remain upright with a cock in her butt.

Finally, after what felt like an eternity of pain, Reynard groaned as he felt his hips flush against Gwendolyn's adolescent ass cheeks, having successfully buried himself balls-deep in the teen's tight ass. He savored the feel of her naked ass pressed against his hips and her virgin bowels tightening around his throbbing manhood.

"Huh…huh…huh…" Gwendolyn panted, straining to look over her shoulder so she could talk more directly to the man with his cock buried in her ass. "I-I-It hurts. So much. It feels like you ripped me apart…"

"It'll get better," Reynard assured her as he reached up and took both of her perky breasts in his hands, groping and massaging them as if hoping to distract the girl from the sodomizing she was about to receive. "Remember, kid, a deal's a deal. Those are the rules."

"Those are the rules," Gwendolyn gasped to herself as she turned back around and bowed her head in hopes of hiding the tears in her eyes. She had agreed to this, whether she had fully realized it at the time or not, and now she had to see it through.

A few minutes later, Gwendolyn was beginning to regret her sense of propriety and fair play as Reynard sawed his dick in and out of her ass seemingly without mercy, going as fast or as hard as he pleased and without any concern as to her own wellbeing. He alternated between gripping her hips and her breasts as they bounced deliciously, each thrust into her tight teenage ass causing her entire body to shake in pain and pleasure.

"Uhn! Uhn! Uhnnn!" Gwendolyn groaned, each thrust burying Reynard's dick deeper and deeper into her bowels until she swore she could feel him thrusting directly into her stomach. She panted for breath, clutching the ground beneath her with everything she had and doing her best to focus on literally anything other than the ass-pounding she was receiving.

Once the girl had finally learned to accommodate the thick stranger in her rectum, a rhythm was established, with Gwendolyn bucking her naked hips back and allowing her asscheeks to bounce against Reynard's hips as he thrust forward and sent his hard cock pounding into the girl's tight anus. Reynard groaned as he felt the girl's bowels tighten around his length, and Gwendolyn hissed and moaned and whimpered as she felt Reynard's girth stroking her insides.

"Told you it would get better," Reynard whispered into Gwendolyn's ear as he bent over her, his hips slamming into her ass, causing her to shiver in both pleasure and pain.

Gwendolyn merely shook her head in response, biting back another scream and trying not to cry as tears of discomfort streamed down her cheeks. It was true she was starting to enjoy it, but she couldn't admit it, not in a thousand years, and the realization humiliate her. Unfortunately, this only caused Reynard to pound into her harder, causing her to cry out in surprise.

"UHNNN!"

With that, Gwendolyn felt her knees and elbows give out, and she collapsed onto the ground until she was lying flat on her stomach with her face and tits pressed against the grass. Reynard didn't lose a beat, and instead released the girl's hips and placed his hands on the ground on either side of her as he continued to fuck her up the ass, but now lying directly on top of her as she squirmed helplessly beneath him.

"Tell me you like it," Reynard commanded her, thrusting his hips into her naked ass again and again, harder than ever before. "Come on, kid, tell me you love it!"

"I – guh – love it!" Gwendolyn gasped, turning her head so she wasn't talking into the dirt.

"What do you love?" Reynard asked.

"Buh, buh, being…fucked!" Gwendolyn answered, fighting back a gentle sob as she found herself pinned to the ground and thoroughly destroyed by the man lying on top of her. "Being…fucked…by yuh, yuh, you!"

"And where do you like being fucked?" Reynard asked again, smiling cruelly.

"I-I-In my…ass!" Gwendolyn hissed, gritting her teeth together as he gave a particularly deep thrust into her tightening rectum. "I like…being fucked…in my ass!"

"Shit, that's good," Reynard moaned as he kept on pounding away. "Say it again, kid."

"Uhnn!" Gwendolyn moaned, still crying gently. "I love it when you fuck my ass!"

"Again!"

"I love it when you fuck my ass!" Gwendolyn moaned loudly, practically screaming. Tears were flowing down her face now, but they were tears of pleasure as well as pain. Despite everything, her body was growing accustomed to what was happening to it, and Gwendolyn was ashamed to find her ass practically _begging_ for more of Reynard's cock. "Oh, Arceusssss…!"

Reynard knew it wouldn't be much longer now. He could feel the pressure rising in his balls, and the sight of the naked teenage girl squirming and sweating in both pain and pleasure beneath him was almost as big of a turn-on as having his cock in her ass in the first place. She was cumming hard, whether she knew it or not, and he was _into_ it.

"Tell me what you want, kid," he groaned as he began jackhammering in and out of Gwendolyn's ass faster than ever before. "Tell me exactly what you want!"

"I want you to cum in me!" Gwendolyn shouted back. She was practically seeing stars at this point, her mind utterly overwhelmed by pain and pleasure. "Cum in my ass! P-P-Please cum in my ass!"

That did it. With a dozen more thrusts and a mighty groan of pleasure, Reynard shoved his dick back into the girl's tight little ass and began firing load after load of his cum deep inside of her, quickly filling her rectum with fiery hot semen. Beneath him, Gwendolyn moaned and shook in ecstasy as she felt Reynard's juices flood and then overflow her adolescent bowels, as though claiming her ass – and the rest of her body – as his personal property from this point forward.

They remained there afterwards, with Reynard practically lying on top of Gwendolyn with his cock still hard up her ass as it slowly began to shrink, the last of his seed successfully deposited inside of her butt. Neither knew how much time passed before they had finally caught their breath and cooled down sufficiently.

"Ohhhh," Gwendolyn whined as she felt Reynard finally pull his dick out of her badly-fucked ass. Her anus puckered the moment he was free, but some of his thick white cum still continued to leak out of it even after.

"Sweet Arceus," Reynard groaned as he fell down onto the grass beneath the girl whose holes he had just thoroughly destroyed. "I swear, kid, you are the best I have _ever_ had. No question."

Despite everything, Gwendolyn smiled a little at the compliment.

"R-Really?" she asked, blushing lightly. "You mean that?"

"Definitely," Reynard confirmed, reaching over and giving the girl's naked ass a playful smack, which only caused her to yelp. "Consider us even, kid."

With that, Reynard stood up and quickly began putting himself back together, with Gwendolyn shortly following suit. Reynard had really only taken off his shirt and pulled down his pants when they began, so it didn't take long for him to dress himself and gather all of his things, whereas he knew Gwendolyn would take a while longer. As such, he took the opportunity of her facing away from him as she put on her bra to slip a few bucks into the kid's backpack; what the hell, he was feeling generous all of a sudden.

 _Still tired, but it's a damn good tired,_ he thought to himself as he stretched and prepared to go on his way. Before he did, though, he took one last look at the girl whose virginity he had stolen (in more than one way).

Though she was holding herself well despite a slight limp, Reynard knew Gwendolyn had to be suffering at least a little bit; he had been the one pounding her, after all, so he knew the girl was certainly sore at the very least. Her face was likewise still flushed, either from the fucking or the embarrassment, and there was a distant look in her eyes as she dressed herself.

 _I might have overdone it a bit_ , he realized. _Of course, now I decide to grow a conscience._

"Hey, kid," he said gently, before correcting himself, "I mean…Gwendolyn."

Gwendolyn looked up; she had just put on her shirt and was in the process of pulling up her skirt when he spoke. "Yeah? You…didn't change your mind, did you?"

"No, you're good," Reynard said with a small smile. "Look, I feel kinda bad for taking advantage of you. So, here, let me walk you back home. It's the least I can do."

Gwendolyn smiled lightly and wiped a tear from her eye. "That's very chivalrous of you."

 _Well, as chivalrous as I can be after cumming in your ass as much as I just did…_

"The thing is, though…" Gwendolyn went on, blushing again and actually looking a little embarrassed. "I was actually gonna ask if you could maybe…take me with you?"

Reynard blinked. "Wait…what?"

"Well, I just started my journey this morning, so I don't really have anywhere to stay," Gwendolyn admitted a little shyly, biting her lip as she did so. "Plus, I don't have any money. So I was thinking maybe you could take me with you? Just for tonight, I mean."

"You…want to come with me?" Reynard asked. Was he hearing her correctly?

"Well, not for free!" Gwendolyn clarified, smiling awkwardly. "I know you would still be paying for a room for the both of us, so you could fuck me again as payment. Or maybe I could try sucking your dick again? I mean, you know…if you want."

Reynard smiled. _If I didn't know better, I'd think a certain someone might have a crush on me. Or at least wants to get fucked again._

"You got a deal, Gwendolyn," he finally said, holding his hand out.

"Thank you," she said with a smile, taking his hand and shaking in confirmation. "And…maybe we can make another deal tomorrow? Or something? I still have a long way to go as a trainer and, well….I would _love_ to have someone to show me the ropes."

"In exchange for something, I imagine," Reynard commented, raising a questioning eyebrow. "Those are the rules, after all."

"Of course," Gwendolyn agreed, blushing lightly and biting her lip. "Those are the rules."

Reynard smiled. "You know, Gwendolyn, I think this might be the beginning of a beautiful relationship."

Gwendolyn giggled. "I'd like that."

"Where are you from, anyway?" Reynard asked.

"Viridian City!" Gwendolyn answered proudly as she slung her backpack over her shoulder.

 _Of course she is_ , Reynard thought with an inward groan as he began leading the girl towards Pallet Town. _I ought to fuck her ass again tonight just for that._


	2. Pallet Town Inn

It was almost ten in the morning by the time Reynard woke up to find himself lying amidst unfamiliar surroundings. This was not particularly surprising; part of being a Pokémon Trainer meant falling asleep and waking up in odd places, sometimes outside, sometimes inside, so Reynard wasn't much taken aback by the fact he didn't recognize where he was at first.

What _did_ catch him by surprise was the naked fourteen-year-old girl lying beside him, still fast asleep, her bright red hair strewn about her pillow.

It took a moment before memories of the previous evening finally returned to him: leaving Viridian City, running into Gwendolyn, battling Gwendolyn, _fucking the living hell out of Gwendolyn_ …

"Good times," Reynard said quietly as he smiled down at the girl currently cuddling into his side, naked as the day she was born and more than likely quite sore after the previous evening's festivities.

The two had made their way to Pallet Town together after Gwendolyn had successfully paid Reynard what she owed, the young man having agreed to let the girl tag along for the time being. It being her first day as a Pokémon Trainer (and clearly not a great one), she had no place to spend the night and not a single dollar to her name. Reynard figured letting her join him for the evening was the least he could do, especially considering everything he had done to her.

It had been almost ten o'clock at night by the time Reynard and Gwendolyn had located Pallet Town's lone inn. From there, it was up to Reynard to procure a room for the two of them, what with Gwendolyn still being flat broke.

"Room for two," Reynard had told the innkeeper as Gwendolyn stood next to him.

"Two beds, I presume?" the old innkeeper had asked.

"Single, please!" Gwendolyn had spoken up, earning her an odd look from both Reynard and the innkeeper, albeit for completely different reasons. She had blushed deeply upon realizing what she had said, but tried to cover it up with a cute and innocent smile.

 _Sounds like someone is a little eager for Round Two_ , Reynard thought to himself as he paid for their room. The innkeeper had glared at the two of them suspiciously, but said nothing else as he handed Reynard the key and sent them on their way.

"So…single bed, huh?" Reynard had asked with a smirk as he opened the door to their modest room and let Gwendolyn in first, chivalrous as always.

"I…didn't want you to waste money on a second bed if we aren't going to use it," Gwendolyn had responded after a few seconds, blushing lightly at the implication as she watched Reynard close the door behind them. "Thank you for letting me spend the night with you, by the way. It really means a lot to me."

"Well, it's not like I don't get anything out of it," Reynard had reminded her with a smirk as he deposited his backpack and supplies on the floor beside the room's single bed. "You did say you'd pay me back, after all. Those are the rules."

"Those are the rules," Gwendolyn had repeated, biting her lip as she turned to face Reynard, revealing her cheeks were still burning red. Her cheeks grew even redder still when she saw Reynard was already taking off his clothes. "Um…what are you doing?"

"Claiming my payment," Reynard answered simply as he stripped himself of his clothes and stood before her entirely naked.

"Wait, right _now_?"

"No time like the present," Reynard told the girl as he took hold of her shirt and began lifting it up over her head, leaving her clad in only her B-cup bra.

"I-If you say so," Gwendolyn said shyly, feeling suddenly exposed without her shirt. "Just…be gentle, okay?"

"No promises."

Two minutes later, Gwendolyn was completely naked and lying on her stomach on the room's single bed as Reynard slammed his cock into her already-sore ass for the second time that evening.

"Ah, ah, ah, ahhh!" Gwendolyn had gasped and moaned as she felt Reynard pound in and out of her adolescent ass like it belonged to him, her fingers clutching at the bed sheets as every thrust slammed her into the mattress below. Reynard fucked her like a man possessed, as though his only wish and desire in the entire world was to make the poor girl as sore as possible before filling her with his hot cum. "Ohhhh, _Arceus_!"

"You feel just as tight as the first time," Reynard had told her as he reached down to grope one of the teenager's B-cup breasts, pressed as they were into the mattress as he fucked her up the ass. "I swear I could get used to this."

"Did you – uhn! – have to – oh! – p-p-put it in my butt again?" Gwendolyn asked beneath him, doing her level best to keep from biting the pillow as she felt Reynard bury his cock deeper and deeper into her ass with every thrust. "It – ow! – it hurts!"

Reynard grinned as he continued to thrust into the naked adolescent girl writhing in pain and pleasure beneath him. "Come on, kid, don't pretend you're not enjoying yourself."

"I'm – uhn! – I'm not!" Gwendolyn lied, blushing deeply as she bucked her bare hips back towards the young man sodomizing her in a desperate attempt to take his cock deeper still into her needy anus. "This is just puh, puh, payment!"

"Admit it, kid…you love it," Reynard had said then, leaning down and whispering into the girl's ear as he stuffed her full of his meat, causing her to shiver in pleasure. "You loved it the first time we did this and you love it even more now. Say it!"

"Nuh, nuh, never!" the girl declared, stifling a moan as she felt her lover push himself balls-deep into her ass, filling her bowels with his thick cock and sending wave after wave of both pain and pleasure surging through her nubile form.

"Say it, kid! Say you love being fucked!" Reynard ordered, slamming into the girl with renewed vigor, determined to fill her to the brim with his cum.

"No!" Gwendolyn groaned, tearing up as she felt Reynard double his efforts on her sore ass.

"Say it!"

"Nuh, nuh, no!"

"Say it!"

"I-I-I love it!" Gwendolyn finally admitted, squeezing her eyes closed as she bucked her naked hips back towards Reynard, savoring the feel of his larger body dominating her tiny one and his thick meat stretching the walls of her adolescent anus. "I luh, luh, love being fucked!"

"Where do you love being fucked?" Reynard asked, grinning to himself but also sweating profusely as he knew his end was approaching.

"In my ass!" Gwendolyn gasped loudly, squirming in pain and pleasure as her orgasm overtook her and Reynard continued to ram into her without mercy. "I love it when you fuck my ass!"

"Fuck yeah, you do," Reynard said with another knowing smirk. "Shit, I'm almost there, kid. Tell me what you want! What do you want more than anything?"

"I want your cuh, cuh, _cum_!" Gwendolyn practically screamed, her entire body still writhing in ecstasy as she felt Reynard plunge deeper and harder into her tight little ass, savoring every single inch of his meat burying itself into her again and again. "I want your cum in my ass, Reynard! Please! I need it! P-P-Please cum in my ass!"

It didn't take long after that. Less than a dozen thrusts later, Reynard groaned loudly as he unloaded into Gwendolyn's fourteen-year-old ass for the second time that evening, filling her bowels with his seed. Beneath him, the girl continued to squirm in pleasure as Reynard unleashed a veritable river of his cum inside of her.

"Ohhhhh," Gwendolyn gasped as she felt Reynard's warm juices fill and then overfill her sore anus. Her entire body was covered in sweat and there were tears in her eyes, but Reynard had been right; much as she hated to admit it, she had grown to love the feel of the older trainer fucking her silly, and was already looking forward to when next he would penetrate her.

After a few moments of rest, Reynard slowly pulled his cock out of Gwendolyn's tightening anus, causing the girl to gasp and hiss lightly in pain and loss, already missing the sensation of being so completely filled. He collapsed next to her in bed a moment later, just as naked as she was, and sweating even more profusely.

"Are you okay?" Gwendolyn asked after giving Reynard a chance to catch his breath. She was still lying on her stomach, far too tired and too sore to do much of anything else.

"Yeah, I'm good, kid," Reynard said as he looked over at the naked girl beside him with a weary smile, even going so far as to reach down and squeeze her tender ass. "You just wear me out."

Gwendolyn blushed at that, almost burying her burning face into the pillow at the compliment. "Do you still think I'm the best you've ever had?"

"Without a doubt," Reynard had reassured her, smiling when he saw her stifle a yawn. "Tired?"

"Mm-hm," the girl confirmed, nodding lightly before scooting closer to Reynard and lying her weary head on his chest. "Think I'm gonna go to sleep. Night."

"Night, kid," Reynard had replied with a chuckle, wrapping an arm around the girl's nude form before he too drifted off to sleep. It had been a big day, after all, and he was frankly surprised he had managed to stay up for as long as he did.

 _Probably explains why it's so late,_ Reynard thought to himself as he checked the clock to find he had been asleep for almost eleven whole hours. _Either that, or the pleasurable company._

Though he was now wide awake and raring to get up and continue his adventure, Reynard couldn't help but take a few moments to admire the naked beauty lying in bed with him. He had known the girl for less than a day, yet he had already fucked her silly a grand total of three times, and it was easy to see why. Gwendolyn might have been a spoiled brat, but she had the goods to pay for her mouth, and Reynard was determined to make her pay as much as possible by the time they next parted ways.

Brushing aside some of the girl's bright red hair, Reynard allowed his rough fingers to travel down over Gwendolyn's bare shoulders, trace a line down her back all the way to her naked ass, which he couldn't help but fondle affectionately, fondly remembering how he had successfully stuffed it full of his meat only the night before. The girl's breasts were pressed up against him, and he could feel her perky nipples hardening at his touch.

"Mmmm," Gwendolyn moaned lightly as she finally began to wake up, her eyes fluttering open as she took in her surroundings and tried to remember where she was and what was going on. "Reynard…?"

"Hey, kid," Reynard answered with a small smile, squeezing her ass lightly and trying not to think about how adorable she looked as she woke up. He almost chuckled as he saw her blush a deep red upon realizing she was practically cuddling up to him in bed. "How do you feel?"

"Sore," Gwendolyn admitted after a moment, her cheeks still a bright red.

 _Sounds about right_ , Reynard thought.

"You okay?" he asked out loud, raising an eyebrow as he noticed how uncomfortable the girl seemed. "Something wrong?"

"No, it's just…we're _naked_ ," Gwendolyn said, whispering the last word as if she was admitting some kind of dirty secret. "And I've…I've never woken up in bed next to a boy before. It's…weird."

"Well, you are a Pokémon Trainer now," Reynard pointed out, "you're going to have to get used to waking up in strange places. I once feel asleep in a cave and woke up to find myself surrounded by angry Kangaskhan. Not a fun morning."

"Really?" Gwendolyn asked, giggling lightly, still blushing a deep red. "I thought Kangaskhan only lived in the Safari Zone? Have you been there?"

"I've been pretty much everywhere in Kanto," Reynard admitted. "Hell, the only reason you ran into me yesterday was because I was looking for the Viridian City Gym Leader so I could get my last badge and head to the Pokémon League."

Gwendolyn's eyes widened at that, and Reynard had to stifle a grin as he realized how impressed the girl looked, like she was meeting a celebrity instead of some random Trainer. "Wait…you already have _seven_ badges? That's incredible!"

"I guess," Reynard agreed with a light shrug and a small smile. "I've been a Trainer for almost a year now. It just takes time and effort. You'll get there, too."

"I don't know about _that_ …" Gwendolyn answered, averting her eyes and blushing again. "I wanted to become a trainer so I could see the world, catch Pokémon, become the best there ever was. But after yesterday…I'm not really sure I'm cut out to be a Pokémon Trainer anymore."

"Of course you are," Reynard reassured her, reaching down and giving her bare ass a light squeeze, causing her to shiver next to him. "You made a mistake yesterday. We all do. I've lost more battles than I can count. The important thing is that you don't give up. You're going to be a great Pokémon Trainer one day, Gwendolyn, I just know it."

"R-Really?" Gwendolyn asked, blushing deeply and once again looking like she might bury her head in Reynard's chest out of embarrassment. "You think I can be as good as you someday?"

"I don't think so, I _know_ so," Reynard said with a smile. "Stick with me, kid, and we'll have you winning battles in no time. I have a few tricks up my sleeve I could teach you."

Gwendolyn smiled. "I'd like that. A lot."

The two laid there in bed together for a few minutes after that, merely resting and enjoying the other's company. Having slept almost eleven hours _and_ thoroughly fucked the most beautiful girl he had ever seen three times in a row the night before, Reynard was feeling pretty good about himself and how his life was going. Gwendolyn, for the most part, merely seemed comfortable cuddling into his side like he was a big teddy bear, albeit one with a large and unforgiving cock. Eventually, however, the fourteen-year-old made to get up and out of bed, causing Reynard to look up and watch as she stretched her nubile form.

"I'm going to take a shower," Gwendolyn told him as she brushed some of her red hair out of her eyes. "I mean…if that's okay."

"Go ahead," Reynard said with a smile, nodding towards the small bathroom. "This is your room just as much as it's mine."

Gwendolyn's only response was to smile and nod at him before bending down to pull some toiletries out of her backpack, inadvertently exposing her bare ass to Reynard, who once again felt a stirring in his loins as he watched the adolescent girl rifle through her belongings. Once she had everything she needed, however, the girl practically pranced off into the bathroom. A moment later, the water started running, and Reynard knew she had stepped into the shower.

That's when he got an idea.

Gwendolyn practically shivered in delight as she felt the warm water of the shower fall upon her naked form. After a full day of adventuring, being mercilessly fucked, and then sleeping in the nude, the girl felt like she needed a shower more than food. She closed her eyes and ran her hands through her long, red hair, losing herself in the heat and steam of the shower.

Her first day as a Pokémon Trainer hadn't exactly gone to plan, that much was obvious. She certainly hadn't been planning on losing her virginity to a stranger before she even caught her second Pokémon, after all. And, though Reynard had been kind enough to heal her Jigglypuff after his Nidoqueen stomped it flat, Gwendolyn knew only amateurs went about without a full team of Pokémon at their disposal, and she was determined to be better than that.

 _Maybe I'm not cut out for this kind of life_ , Gwendolyn thought to herself sadly as she wiped some of the sweat and grime off her nubile form, being sure to clean her breasts, pussy, and ass after Reynard's rough manhandling of them all. _Reynard says he thinks I can be a great Trainer, but what if he's just saying that? I mean, he's cute, and kinda charming, and a really good Trainer, but…can I really trust him? Maybe I should just head back home…_

Gwendolyn sighed as she finished washing her hair, squeezing out the last of the shampoo she had brought from home. As tempting as it might have sounded, she knew she couldn't head back home, not now, not so soon after leaving. So what, then, could she do?

"Hey, smells great in here. What is that, Pinap Berry shampoo?"

"Reynard?" Gwendolyn squealed, almost slipping on the wet floor as she spun around to find the older Trainer standing in the shower right behind her, having apparently slipped in while she was deep in thought. She instinctively tried to hide her nakedness by covering her breasts and squeezing her legs closed despite the fact Reynard had already seen everything the night before. "W-W-What are you doing?"

The older Trainer just smiled a little at first, that tiny smirk that both infuriated Gwendolyn and sent a shiver of pleasure running down her spine as she knew he was taking in her naked form. He was likewise fully nude as he stood before her, arms and legs toned from his adventuring around Kanto and his cock hanging lewdly between his legs, already semi-erect at the look of the pubescent girl in front of him; Gwendolyn tried to ignore how her mouth watered at the mere sight of it.

"What does it look like I'm doing?" Reynard asked with his usual cocky smile as he too stepped into the warm shower, inadvertently causing Gwendolyn to back up a little. "I'm taking a shower. Figured I would join you."

"You could have just waited," Gwendolyn told him, pouting visibly as she continued to cover her breasts with her hands and arms. Her cheeks were bright red and only growing redder. "I'm still not used to being seen like this…"

"What, naked?" Reynard asked, laughing slightly. "Get used to it, kid, I've already seen everything you have at this point. And besides…I _really_ like what I see."

"R-Really?" Gwendolyn asked, her cheeks burning under the warm water of the shower. No matter how often Reynard complimented her body, she still found it made her melt like a schoolgirl talking to her first crush. "I'll bet you're just saying that because you want to fuck me again…"

"Eh, a little from column A, a little from column B," Reynard admitted, once again flashing his cocky smirk as he began to wash himself under the shower. "You're beautiful, kid. Really. A bit of a brat and a little naïve, maybe, but definitely hot as hell. I mean, I wouldn't have made that bet with you the other day if I thought you didn't have the goods."

Gwendolyn only continued to blush. "I…I guess not…"

"Speaking of," Reynard said as he continued to clean himself, "how are you feeling? Any better? Less sore?"

"A little," Gwendolyn admitted shyly, still trying to process everything. "My butt still hurts, but other than that…I guess I feel okay."

"Good," Reynard commented with a smile, "because I was thinking now might be a good time to make another _deal_."

With that, the young man slowly reached down, took hold of Gwendolyn's arms, and gently moved them away from her chest, revealing her perky breasts to him and causing her to blush an even deeper shade of red. Still smiling, Reynard then moved his one hand down the girl's bare stomach, causing her to shiver lightly, before reaching even lower still and then slowly running his fingers over the girl's tight pussy.

"Huh!" Gwendolyn gasped lightly, fighting the urge to both close her legs and push her cunt further into Reynard's hand at the same time. "R-Reynard?"

"You did say you wanted to make another deal last night, right?" Reynard asked as he slowly stroked Gwendolyn's glistening lips.

"Y-Yes," Gwendolyn nodded, whimpering slightly as she looked up at the man fondling her.

"And you want to become a great Pokémon Trainer, right?" Reynard continued, both in speaking and in stroking.

"More than anything," Gwendolyn admitted, shyly placing one of her hands on Reynard's toned chest as he slowly slipped a single finger inside of her. "Oh! Oh, Arceus…"

"So why don't we just make it easy and official?" Reynard asked, gently moving his finger inside of Gwendolyn's cunt and taking a great deal of pleasure in watching her squirm in front of him. "I show you the ropes – how to catch Pokémon, how to battle, how to train – and, in return, I get _you_. All of you."

"A-All of me?" Gwendolyn asked shakily, looking up into Reynard's eyes as she tried to catch her breath with his finger inside of her.

" _All_ of you," Reynard repeated. "We can set up the ground rules later, but in the meantime…what do you say?"

With that, he slowly pushed a second finger into Gwendolyn's cunt, causing her eyes to gasp loudly and her eyes to widen as he stretched her from the inside out.

"Do we have a deal?"

"Y-Yes!" Gwendolyn finally proclaimed, now practically shaking with pleasure as she felt Reynard moving inside of her. "Yes, please, just…just do it, Reynard!"

"Do what?" Reynard asked mischievously.

"Fuck me!" Gwendolyn exclaimed, desperation in her eyes as she looked up at him. "Please, Reynard, just fuck me already!"

Reynard, ever the gentleman, wasted no time in obeying the girl's command. He spun her around so she was facing the shower wall and her ass was pressed up against his cock, already hard and twitching with anticipation. A moment later, Gwendolyn had her hands placed against the slippery shower wall as Reynard entered her from behind, sheathing his thick cock inside of her wet cunt in its entirety right from the beginning."

"Ohhhh, _fuck_!" Gwendolyn cried as she felt Reynard bury himself balls-deep inside of her, his hips pressed against her youthful ass and her pussy wrapped around his cock. It wasn't long before her cries turned into moans of pleasure as Reynard began to push and pull his cock in and out of her adolescent pussy, stroking her insides with his thick meat and driving her ever closer to the brink of maddening pleasure.

Reynard smiled and closed his eyes, savoring the sensation of Gwendolyn's impossibly tight cunt wrapped around his cock as he shoved himself in and out of her, his hands grapping her nubile hips and holding her still as he pounded her pussy. The height difference between them meant that Reynard had to bend over somewhat in order to slam into the girl at just the right angle, but it was worth it.

"I'm never gonna get tired of this," the older trainer commented as he drove himself in and out of the teenage girl, his balls slapping against the lips of her pussy as he thrust back and forth.

"Muh, muh, me, neither!" Gwendolyn admitted as she tried to buck her hips back at Reynard, trying to take as much of his dick as she possibly could, as though no length or girth would ever be enough to fully satisfy her now that she had been with him. "Uhn! Uhn! Uhnnn! Fuck! Yes! Fuh, fuh, fuck me!"

 _Sounds like someone is starting to get used to this_ , Reynard thought to himself as he reached up to fondle one of the girl's beautiful breasts as it bounced back and forth deliciously in time with his thrusts into her cunt. _I have a feeling this is gonna end up being the best deal I ever made_.

Eventually, Reynard was fucking Gwendolyn so hard that he was practically lifting her off the ground, forcing her arms to bend at the elbows as he pushed her closer and closer to the shower wall, having lost all restraint. Soon enough, Gwendolyn was standing on her toes just to keep Reynard's cock lodged inside of her, and she was pretty sure she would have fallen over completely had he not been holding her up.

 _He's fucking me so hard I can barely keep standing!_ , Gwen thought to herself as Reynard continued to slam into her without all the ferocity of a charging Rhydon. Her perky little tits were bouncing back and forth so much she was almost afraid they were going to fly off.

"Guh, huh, huh!" the fourteen-year-old panted and gasped as she felt Reynard slam into her again and again and again, fucking all the sense out of her. Were he going any faster or any harder, Gwendolyn was afraid her eyes might have been rolling back into her head and her tongue would be hanging out of her mouth. "Soooo good…"

The two of them went on like that for several minutes, each of them growing closer and closer to orgasm as they tried to meet the other thrust for thrust. Reynard would shove forward, burying the entirety of his cock inside of Gwendolyn, who would scream and squirm in pleasure before bucking herself back at him, slapping her bare asscheeks against his hips to spur him on, daring him to pound her harder and faster still. For being a virgin only a day before, the girl was learning quickly, and that was much to Reynard's benefit.

"Ruh, ruh, Reynard?" Gwendolyn suddenly asked, turning her head so she could at least glance at the man fucking her brains out. "Can I – oh! Uhn! – ask something?"

"What's up?" Reynard asked, still thrusting into her, but slower now, to allow the girl to speak without interrupting her every half-second as he plunged inside of her at breakneck speed. "You getting sore again?"

"N-No," Gwendolyn said as she continued to buck her naked hips back at her lover. "W-W-Well, yeah, but…I kinda like it. I was wondering if we could, um…"

"Yeah?"

"Can I…turn around?" Gwendolyn finally managed to ask, her cheeks red from embarrassment just as much as the rough activity she and Reynard were engaging in. "I like this – a lot! – but…I want to face you. If that's okay."

 _Someone definitely has a crush on me_ , Reynard thought with a gentle smile, running a hand up the girl's back and then moving some of her wet red hair out of the way.

"Sure thing, kid," he finally said as he slowly pulled his cock out from inside of her, causing the girl to gasp lightly at his exit and allowing her to stand back up straight for the first time since they started fucking. "Let's see that beautiful face of yours."

Blushing deeply from the man's compliment, Gwendolyn slowly turned around so she was facing Reynard, albeit on shaking legs that felt like they could give out any minute. Luckily for her, Reynard knew what to do; reaching around her, he took hold of the girl by her ass and lifted her up into his arms. Gasping at his touch and sudden strength, Gwendolyn responded by spreading her weak legs and then wrapping them around Reynard's waist until her pussy was hovering only centimeters above his throbbing cock. To better help keep his own balance, Reynard pushed Gwendolyn's back up against the shower wall as he prepared to lower her back down onto his waiting dick.

"Ready?" he asked, looking into the girl's green eyes as he held her up by her perfectly round ass, pressing her against the shower wall, feeling the heat of her cunt radiating from between her legs.

"Do it," Gwendolyn told him, tightening her legs around his waist. "Fuck me, Reynard!"

With that, Reynard slowly lowered Gwendolyn onto his cock, gasping as he felt the swollen head of his dick push apart her adolescent pussy lips and then bury its girth deeper and deeper into the thick folds of her cunt. Gwendolyn moaned and groaned in both pain and pleasure as she felt Reynard's thick cock push itself deeper and deeper inside of her until she felt so full it was almost difficult to breathe.

After a moment of allowing Gwendolyn to adjust to his size in this position, Reynard slowly began to pull his dick back out of her…before slamming it into her once again, all the way, burying himself balls-deep inside of the girl.

"HUH!" Gwendolyn groaned loudly, her eyes closing as she felt her lover take her for all she was worth. Reynard began thrusting in and out of her again after that, squeezing her tight little ass as he fucked her against the shower wall. "Aah! Aah! Uhnnn! Oh, _Arceus_!"

It wasn't long before the two of them were back to where they had been mere minutes before, with Reynard slamming into Gwendolyn with everything he had and the girl bucking her naked hips back at him with the last of her strength and energy. Reynard slammed his cock into Gwendolyn's impossibly tight pussy again and again and again, savoring the feel of her naked hips slapping against his as he drove himself deeper into her with every thrust. He took great pleasure from the sight of the teenager's perky breasts bouncing wildly up and down as a result of their desperate movements, only further exciting him all the more and encouraging him to give Gwendolyn everything he had.

Gwendolyn, meanwhile, gripped the slippery wall of the shower behind her as Reynard fucked her against it and her youthful breasts bounced up and down delightfully with every thrust. She tightened her legs around Reynard's waist, not just to keep herself from falling, but to feel him deeper and deeper inside of her. She squirmed and bucked and moaned and did all she could just to respond to the pounding her lover was giving her, doing all she could to milk every ounce of pleasure out of the experience as possible.

"You're getting _really_ good at this," Reynard told her breathlessly as he continued to drill his cock into Gwendolyn's needy cunt.

"You really thuh, thuh, think so?" Gwendolyn asked shyly, her cheeks burning red and with tears in her eyes as she looked at the man pounding her into the shower wall.

"Definitely," Reynard responded, once again flashing his cocky grin as he gave a particularly deep thrust into the girl, causing her to yelp in both pain and pleasure.

"Still think I'm the buh, buh, best you've ever had?" Gwendolyn continued. She lowered one of her hands as she asked, placing it on top of Reynard's hand as he clutched her nubile ass.

"Not a doubt," Reynard said, tightening his grip on her ass and even going so far as to use one of his free fingers to stroke the teenager's puckered anus.

Maybe it was Reynard's compliment, maybe it was his finger circling her asshole, maybe it was just the friction building up inside of her, but that was the moment when Gwendolyn finally felt her body give in to the pleasure. She screamed and tightened her legs around Reynard's waist as her orgasm wracked her body, sending an overpowering tingling sensation throughout her entire form and causing her to shake almost uncontrollably.

"UUHN!" Gwendolyn shrieked as she felt Reynard's cock pounding inside of her, sending wave after wave of pleasure surging through her. "Oh, Reynard! Oh, Arceus! Oh, _fuuuuck_!"

It wasn't long after both witnessing and feeling Gwendolyn's orgasm that Reynard knew his own was coming. Knowing the girl had been worried of pregnancy the day before, he waited until just the moment before he felt like he was going to burst before pulling himself out of Gwendolyn and then erupting all over her. The girl was still coming down from her own orgasm when she felt Reynard's cum splattering onto her, coating her stomach and breasts in a thin layer of her lover's juices.

"Sorry," Reynard said as he helped Gwendolyn stand back up, albeit on unsteady legs. "Figured it was better than finishing inside of you."

"It's okay," Gwendolyn replied as she smiled weakly at him and then stood beneath the stream of hot water still coming from the showerhead, already feeling Reynard's cum being washed off her body. "At least this time we're in the shower."

With that, the two of them proceeded to rinse themselves off and finish their respective showers, especially considering they were now just as dirty as they had been when they entered. It was another ten minutes or so before they finally turned the shower off and emerged into the steamy bathroom to dry themselves off. Finishing first, Reynard wrapped his towel around his waist and then exited the bathroom, determined to find something to wear before they went out and officially started their journey together.

As such, he was a little shocked when he heard the bathroom door open and saw Gwendolyn emerge from out of the steam, still drying her wet red hair but otherwise as naked as the day she was born, her entire body out for show.

"Looks like someone finally got over that fear of being seen naked," Reynard commented as Gwendolyn walked into the bedroom and began heading towards her things so she could change.

"Well…like you said," Gwendolyn admitted with a blush, "you've already seen me. And you said you liked what you saw."

"I did," Reynard said with a smile. "Still do."

Gwendolyn blushed again. "So, um, this deal…you're really going to help me become a better Pokémon Trainer? You weren't just saying that?"

"I never go back on a deal, kid," Reynard told her as he finished getting dressed. "I scratch your back, you scratch mine. Not like I have anything better to do with the Viridian City Gym closed anyway. Besides…I'm starting to like you."

"I'm…starting to like you, too," Gwendolyn said, still blushing deeply, but now smiling a little as well. "So, what do we do now?"

"Now? Now you get some clothes on and we check outta here," Reynard told her with renewed confidence. "We have a long way to go to whip you into shape, kid. Just follow my lead and you'll do great. Those are the rules."

"Yes, sir!" Gwendolyn responded with a fake salute and a giggle. With that, she practically danced over to her things in order to get dressed, once again bending over and inadvertently exposing her bare ass to Reynard just as she had done before she entered the shower.

 _No, come on, it's already late enough,_ Reynard told himself as he felt that familiar stirring in his loins upon gazing Gwendolyn practically mooning him. _We have plenty of time for that later. Besides, she's probably worn out. Give her a break._

Then Gwendolyn started wriggling her butt back and forth slightly, as though dancing in tune to a rhythm only she could hear, and Reynard felt the last of his resolve fade away.

 _Well, maybe one last fuck before we leave…_


End file.
